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AR057010A1 - PROCEDURES TO PREPARE DERIVATIVES OF BENCIL-BENZENE SUSTIUATED WITH GLUCOPIRANOSIL, ITS INTERMEDIATE PRODUCTS AND METHODS OF OBTAINING THEMSELVES. - Google Patents

PROCEDURES TO PREPARE DERIVATIVES OF BENCIL-BENZENE SUSTIUATED WITH GLUCOPIRANOSIL, ITS INTERMEDIATE PRODUCTS AND METHODS OF OBTAINING THEMSELVES.

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Publication number
AR057010A1
AR057010A1ARP060101865AARP060101865AAR057010A1AR 057010 A1AR057010 A1AR 057010A1AR P060101865 AARP060101865 AAR P060101865AAR P060101865 AARP060101865 AAR P060101865AAR 057010 A1AR057010 A1AR 057010A1
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Argentina
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alkyl
aryl
groups
carbonyl
tetrahydrofuran
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ARP060101865A
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Spanish (es)
Inventor
Matthias Eckhardt
Frank Himmelsbach
Xiao Jun Wang
Wenjun Tang
Xiufeng Sun
Li Zhang
Dhileepkumar Krishnamurthy
Chris H Senanayake
Zhengxu Han
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Boehringer Ingelheim Int
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Application filed by Boehringer Ingelheim IntfiledCriticalBoehringer Ingelheim Int
Publication of AR057010A1publicationCriticalpatent/AR057010A1/en

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Translated fromSpanish

Procedimiento para preparar los compuestos de la formula general (1) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R2 significa tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y R3 significa H; caracterizado porque un compuesto de formula general (2) en donde R1 se define como antes en esta memoria y R2, independientemente uno de otro, significa H, (alquil C1-18)carbonilo, (alquil C1-18)oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo, aril- alquilo C1-3, alilo, RaRbRcSi, CRaRbORc, en donde dos grupos R2 adyacentes pueden estar enlazados uno con otro para formar un grupo de puenteo SiRaRb, CRaRb o CRaORb-CRaORb; con la condicion de que al menos un sustituyentes R2 no sea H; Ra, Rb, Rc, independientemente entre sí, significan alquilo C1-4, arilo o aril-alquilo C1-3, en los que los grupos alquilo pueden estar mono- o poli-sustituidos con halogeno; L1, independientemente uno de otro, se seleccionan entre F, Cl, Br, alquilo C1-3, alcoxi C1-4 y nitro; mientras que por los grupos arilo mencionados en la definicion de los grupos anteriores se quieren dar a entender grupos fenilo o naftilo, que pueden estar mono- o poli-sustituidos con L1; se escinden los grupos R2 protectores que no sean H. Además, se refiere a compuestos intermedios obtenidos en estos procedimientos y métodos de preparacion de éstos. Reivindicacion 3: Procedimiento para preparar los compuestos de formula general (3) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y R2, independientemente uno de otro, significa H, (alquil C1-18)carbonilo, (alquil C1-18)oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo, aril-alquilo C1-3, alilo, RaRbRcSi, CRaRbORc, en donde dos grupos R2 adyacentes pueden estar enlazados uno con otro para formar un grupo de puenteo SiRaRb, CRaRb o CRaORb-CRaORb; R' significa H, alquilo C1-6, (alquil C1-4)carbonilo, (alquil C1-4)- oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo; Ra, Rb, Rc, independientemente entre sí, significan alquilo C1-4, arilo o aril-alquilo C1-3, en los que los grupos alquilo pueden estar mono- o poli-sustituidos con halogeno; L1, independientemente uno de otro, se seleccionan entre F, Cl, Br, alquilo C1-3, alcoxi C1-4 y nitro; mientras que por los grupos arilo mencionados en la definicion de los grupos anteriores se quieren dar a entender grupos fenilo o naftilo, que pueden estar mono- o poli-sustituidos con L1; caracterizado porque un compuesto organometálico de la formula (6) en donde R1 se define como antes en eta memoria y M significa Li o MgHal, en donde Hal significa Cl, Br o I; o un derivado de mismo obtenido por transmetalacion; compuesto de la formula (6) que se puede obtener mediante intercambio halogeno-metal o mediante la insercion de un metal en el enlace carbono-halogeno de un compuesto de halogeno-bencilbenceno de la formula general (5) en donde R1 se define como antes en esta memoria y X significa Br o I; y, opcionalmente, subsiguiente transmetalacion, se anade a una gluconolactona de la formula general (4) en donde R2 es como se define antes en esta memoria, luego el aducto obtenido se hace reaccionar con agua o un alcohol R'-OH, en que R' significa alquilo C1-6, en presencia de un ácido y, opcionalmente, el producto obtenido en la reaccion con agua, en donde R' significa H, se convierte, en una reaccion subsiguiente con un agente acilante, en el producto de formula (3), en donde R' significa (alquil C1-4)carbonilo, (alquil C1-4)-oxicarbonilo, arilcarbonilo o aril-alquil C1-4)-carbonilo, en donde el término öariloö se define como antes en esta memoria. Reivindicacion 12: Compuesto de formula general (2) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y R2, independientemente uno de otro, significa H, (alquil C1-18)carbonilo, (alquil C1-18)oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo, aril-alquilo C1-3, alilo, RaRbRcSi, CRaRbORc, en donde dos grupos R2 adyacentes pueden estar enlazados uno con otro para formar un grupo de puenteo SiRaRb, CRaRb o CRaORb- CRaORb; con la condicion de que al menos un sustituyentes R2 no signifique H; Ra, Rb, Rc, independientemente entre sí, significan alquilo C1-4, arilo o aril-alquilo C1-3, en los que los grupos alquilo pueden estar mono- o poli-sustituidos con halogeno; L1, independientemente uno de otro, se seleccionan entre F, Cl, Br, alquilo C1-3, alcoxi C1-4 y nitro; mientras que por los grupos arilo mencionados en la definicion de los grupos anteriores se quieren dar a entender grupos fenilo o naftilo, que pueden estar mono- o poli-sustituidos con L1. Reivindicacion 15: Compuesto de formula general 3) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y R2, independientemente uno de otro, significa H, (alquil C1-18)carbonilo, (alquil C1-18)oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo, aril-alquilo C1-3, alilo, RaRbRcSi, CRaRbORc, en donde dos grupos R2 adyacentes pueden estar enlazados uno con otro para formar un grupo de puenteo SiRaRb, CRaRb o CRaORb-CRaORb; Ra, Rb, Rc, independientemente entre sí, significan alquilo C1-4, arilo o aril-alquilo C1-3, en los que los grupos alquilo pueden estar mono- o poli-sustituidos con halogeno; L1, independientemente uno de otro, se seleccionan entre F, Cl, Br, alquilo C1-3, alcoxi C1-4 y nitro; R' significa H, alquilo C1-6, (alquil C1-4)carbonilo, (alquil C1-4)-oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo; mientras que por los grupos arilo mencionados en la definicion de los grupos anteriores se quieren dar a entender grupos fenilo o naftilo, que pueden estar mono- o poli-sustituidos con L1; Reivindicacion 18: Compuesto de formula general (6) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y M significa Li o MgHal, en donde Hal significa Cl, Br o I. Reivindicacion 19: Compuesto de formula general (5) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y X significa Br o I. Reivindicacion 21: Compuesto de formula general (7) o de la formula (9) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y X significa Br o I. Reivindicacion 23:Compuesto de formula general (26) en la que X significa Br o I; y Z significa hidroxi, F, Cl, Br, I, alquil C1-4-sulfoniloxi, arilsulfoniloxi, aril-alquil C1-3-sulfoniloxi, di-(alquiloxi C1-6)-boronilo, di-hidroxi-boronilo, KF3B, NaF3B o LiF3B; y L1, independientemente uno de otro, se seleccionan entre F, Cl, Br, alquilo C1-3, alcoxi C1-4 y nitro; mientras que por los grupos arilo mencionados en la definicion de los grupos anteriores se quieren dar a entender grupos fenilo o naftilo, que pueden estar mono- o poli-sustituidos con L1. Reivindicacion 25: Compuesto de formula general (32) en la que R1 significa ciclobutilo, ciclopentilo, ciclohexilo, R-tetrahidrofuran-3-ilo, S-tetrahidrofuran-3-ilo o tetrahidropiran-4-ilo; y R2, independientemente uno de otro, significa H, (alquil C1-18)carbonilo, (alquil C1-18)oxicarbonilo, arilcarbonilo, aril-(alquil C1-3)-carbonilo, aril-alquilo C1-3, alilo, RaRbRcSi, CRaRbORc, en donde dos grupos R2 adyacentes pueden estar enlazados uno con otro para formar un grupo de puenteo SiRaRb, CRaRb o CRaORb-CRaORb; Ra, Rb, Rc, independientemente entre sí, significan alquilo C1-4, arilo o aril-alquilo C1-3, en los que los grupos alquilo pueden estar mono- o poli-sustituidos con halogeno; L1, independientemente uno de otro, se seleccionan entre F, Cl, Br, alquilo C1-3, alcoxi C1-4 y nitro; mientras que por los grupos arilo mencionados en la definicion de los grupos anteriores se quieren dar a entender grupos fenilo o naftilo, que pueden estar mono- o poli-sustituidos con L1.Process for preparing the compounds of the general formula (1) in which R1 means cyclobutyl, cyclopentyl, cyclohexyl, R2 means tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and R3 means H; characterized in that a compound of general formula (2) wherein R1 is defined as hereinbefore and R2, independently of one another, means H, (C1-18 alkyl) carbonyl, (C1-18 alkyl) oxycarbonyl, arylcarbonyl, aryl - (C1-3alkyl) -carbonyl, aryl-C1-3alkyl, allyl, RaRbRcSi, CRaRbORc, wherein two adjacent R2 groups may be linked to each other to form a bridge group SiRaRb, CRaRb or CRaORb-CRaORb; with the proviso that at least one R2 substituents is not H; Ra, Rb, Rc, independently of one another, means C1-4 alkyl, aryl or aryl-C1-3 alkyl, in which the alkyl groups may be mono- or poly-substituted with halogen; L1, independently of one another, is selected from F, Cl, Br, C1-3 alkyl, C1-4 alkoxy and nitro; while by the aryl groups mentioned in the definition of the above groups it is meant phenyl or naphthyl groups, which may be mono- or poly-substituted with L1; R2 protective groups other than H are cleaved. In addition, it refers to intermediate compounds obtained in these processes and methods of preparing them. Claim 3: Process for preparing the compounds of general formula (3) in which R 1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and R2, independently of one another, means H, (C1-18 alkyl) carbonyl, (C1-18 alkyl) oxycarbonyl, arylcarbonyl, aryl- (C1-3 alkyl) -carbonyl, aryl-C1-3 alkyl, allyl, RaRbRcSi , CRaRbORc, wherein two adjacent R2 groups may be linked to each other to form a bridge group SiRaRb, CRaRb or CRaORb-CRaORb; R 'means H, C 1-6 alkyl, (C 1-4 alkyl) carbonyl, (C 1-4 alkyl) -oxycarbonyl, arylcarbonyl, aryl- (C 1-3 alkyl) -carbonyl; Ra, Rb, Rc, independently of one another, means C1-4 alkyl, aryl or aryl-C1-3 alkyl, in which the alkyl groups may be mono- or poly-substituted with halogen; L1, independently of one another, is selected from F, Cl, Br, C1-3 alkyl, C1-4 alkoxy and nitro; while by the aryl groups mentioned in the definition of the above groups it is meant phenyl or naphthyl groups, which may be mono- or poly-substituted with L1; characterized in that an organometallic compound of the formula (6) wherein R1 is defined as before in this memory and M means Li or MgHal, wherein Hal means Cl, Br or I; or a derivative thereof obtained by transmetalation; compound of the formula (6) that can be obtained by halogen-metal exchange or by inserting a metal in the carbon-halogen bond of a halogen-benzylbenzene compound of the general formula (5) wherein R1 is defined as before in this memory and X means Br or I; and, optionally, subsequent transmetalation, is added to a gluconolactone of the general formula (4) wherein R2 is as defined hereinbefore, then the adduct obtained is reacted with water or an R'-OH alcohol, in which R 'means C1-6 alkyl, in the presence of an acid and, optionally, the product obtained in the reaction with water, where R' means H, is converted, in a subsequent reaction with an acylating agent, into the product of formula (3), wherein R 'means (C1-4 alkyl) carbonyl, (C1-4 alkyl) -oxycarbonyl, arylcarbonyl or aryl-C1-4 alkyl) -carbonyl, wherein the term öariloö is defined as hereinbefore . Claim 12: Compound of general formula (2) wherein R 1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and R2, independently of one another, means H, (C1-18 alkyl) carbonyl, (C1-18 alkyl) oxycarbonyl, arylcarbonyl, aryl- (C1-3 alkyl) -carbonyl, aryl-C1-3 alkyl, allyl, RaRbRcSi , CRaRbORc, wherein two adjacent R2 groups may be linked to each other to form a bridge group SiRaRb, CRaRb or CRaORb-CRaORb; with the proviso that at least one R2 substituents does not mean H; Ra, Rb, Rc, independently of one another, means C1-4 alkyl, aryl or aryl-C1-3 alkyl, in which the alkyl groups may be mono- or poly-substituted with halogen; L1, independently of one another, is selected from F, Cl, Br, C1-3 alkyl, C1-4 alkoxy and nitro; while by the aryl groups mentioned in the definition of the above groups it is meant phenyl or naphthyl groups, which may be mono- or poly-substituted with L1. Claim 15: Compound of general formula 3) wherein R1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and R2, independently of one another, means H, (C1-18 alkyl) carbonyl, (C1-18 alkyl) oxycarbonyl, arylcarbonyl, aryl- (C1-3 alkyl) -carbonyl, aryl-C1-3 alkyl, allyl, RaRbRcSi , CRaRbORc, wherein two adjacent R2 groups may be linked to each other to form a bridge group SiRaRb, CRaRb or CRaORb-CRaORb; Ra, Rb, Rc, independently of one another, means C1-4 alkyl, aryl or aryl-C1-3 alkyl, in which the alkyl groups may be mono- or poly-substituted with halogen; L1, independently of one another, is selected from F, Cl, Br, C1-3 alkyl, C1-4 alkoxy and nitro; R 'means H, C1-6 alkyl, (C1-4 alkyl) carbonyl, (C1-4 alkyl) -oxycarbonyl, arylcarbonyl, aryl- (C1-3 alkyl) -carbonyl; while by the aryl groups mentioned in the definition of the above groups it is meant phenyl or naphthyl groups, which may be mono- or poly-substituted with L1; Claim 18: Compound of general formula (6) wherein R1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and M means Li or MgHal, wherein Hal means Cl, Br or I. Claim 19: Compound of general formula (5) wherein R1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran- 3-yl or tetrahydropyran-4-yl; and X means Br or I. Claim 21: Compound of general formula (7) or of formula (9) wherein R1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and X means Br or I. Claim 23: Compound of general formula (26) wherein X means Br or I; and Z means hydroxy, F, Cl, Br, I, C 1-4 alkyl-sulfonyloxy, arylsulfonyloxy, aryl-C 1-3 alkyl sulfonyloxy, di- (C 1-6 alkyloxy) -boronyl, di-hydroxy-boronyl, KF3B, NaF3B or LiF3B; and L1, independently of each other, are selected from F, Cl, Br, C1-3 alkyl, C1-4 alkoxy and nitro; while by the aryl groups mentioned in the definition of the above groups it is meant phenyl or naphthyl groups, which may be mono- or poly-substituted with L1. Claim 25: Compound of general formula (32) wherein R1 means cyclobutyl, cyclopentyl, cyclohexyl, R-tetrahydrofuran-3-yl, S-tetrahydrofuran-3-yl or tetrahydropyran-4-yl; and R2, independently of one another, means H, (C1-18 alkyl) carbonyl, (C1-18 alkyl) oxycarbonyl, arylcarbonyl, aryl- (C1-3 alkyl) -carbonyl, aryl-C1-3 alkyl, allyl, RaRbRcSi , CRaRbORc, wherein two adjacent R2 groups may be linked to each other to form a bridge group SiRaRb, CRaRb or CRaORb-CRaORb; Ra, Rb, Rc, independently of one another, means C1-4 alkyl, aryl or aryl-C1-3 alkyl, in which the alkyl groups may be mono- or poly-substituted with halogen; L1, independently of one another, is selected from F, Cl, Br, C1-3 alkyl, C1-4 alkoxy and nitro; while by the aryl groups mentioned in the definition of the above groups it is meant phenyl or naphthyl groups, which may be mono- or poly-substituted with L1.

ARP060101865A2005-05-102006-05-10 PROCEDURES TO PREPARE DERIVATIVES OF BENCIL-BENZENE SUSTIUATED WITH GLUCOPIRANOSIL, ITS INTERMEDIATE PRODUCTS AND METHODS OF OBTAINING THEMSELVES.AR057010A1 (en)

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AR (1)AR057010A1 (en)
AU (1)AU2006245712B2 (en)
BR (1)BRPI0608603A2 (en)
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EA (1)EA014468B1 (en)
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